CN101372457A - Preparation of alkyl trimethyl quaternary ammonium salt - Google Patents
Preparation of alkyl trimethyl quaternary ammonium salt Download PDFInfo
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- CN101372457A CN101372457A CNA2008101725239A CN200810172523A CN101372457A CN 101372457 A CN101372457 A CN 101372457A CN A2008101725239 A CNA2008101725239 A CN A2008101725239A CN 200810172523 A CN200810172523 A CN 200810172523A CN 101372457 A CN101372457 A CN 101372457A
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- quaternary ammonium
- ammonium salt
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Abstract
A method for preparing alkyl trimethyl quaternary ammonium salt belongs to the technical field of organic compound synthesis. In the preparation method, methyl carbonate is taken as a quaternizing reagent to synthesize monomethyl-carbonate quaternary ammonium salt, and the quaternary ammonium salt with other counter ions is synthesized by hydrolysis reaction or displacement reaction with various acids (alkalis). The preparation method has the advantages of no environmental pollution or toxin residue, and the product prepared by the method is widely applied to the field of daily chemicals and other industrial fields.
Description
Technical field
The present invention relates to a kind of methylcarbonate and synthesize preparation method with novel trans ionic alkyl trimethyl quaternary ammonium salt as quaternizing agent.
Background technology
The prior synthesizing method of alkyl trimethyl quaternary ammonium salt adopts methyl chloride, monobromethane, methyl-sulfate etc. as quaternizing agent mostly, these traditional quaternizing agents have certain toxicity and corrodibility, and the reaction process consumption is big, there is the serious environmental pollution problem, product with these quaternizing agent preparations, have toxic residue to a certain degree, be used for household chemicals, can cause certain injury human body.
Methylcarbonate can replace traditional methylating reagents such as methyl-sulfate, methyl chloride, monobromethane as a kind of novel green Organic Chemicals, can on atoms such as carbon, nitrogen, sulphur, oxygen methylation reaction take place.But in quarternary ammonium salt compound synthetic, methylcarbonate is as quaternizing agent and alkyl dimethyl tertiary amide generation quaterisation, and bibliographical information is less.
Summary of the invention
The objective of the invention is to overcome the toxic deficiency of prior synthesizing method environmental pollution and product residue, provide a kind of nontoxic with methylcarbonate as quaternizing agent carbonate synthesis mono-methyl quaternary ammonium salt, as the synthetic preparation method of raw material with alkyl trimethyl quaternary ammonium salt of other gegenion.
The chemical structural formula of alkyl trimethyl quaternary ammonium salt of the present invention is as follows:
In the formula: R is C
1～C
22Saturated, unsaturated, straight chain, the alkyl of side chain;
A
-Be CH
3CO
3 -, HCO
3 -, HCOO
-, CH
3COO
-, lactate, laurate, cardamom acid group, stearic acid root, HSO
4 -, NO
3 -, H
2PO
4 -, OH
-
Synthetic method of the present invention is to utilize methylcarbonate to generate carbonic acid mono-methyl quaternary ammonium salt as quaternizing agent and alkyl dimethyl tertiary amide reaction, carbonic acid mono-methyl quaternary ammonium salt generation hydrolysis reaction generates bicarbonate quats salt, and carbonic acid mono-methyl quaternary ammonium salt and various organic acid, mineral acid or alkali reaction generate the quaternary ammonium salt with other gegenion.
Described carbonic acid mono-methyl quaternary ammonium salt synthetic be with alkyl dimethyl tertiary amide and methylcarbonate be raw material in reaction kettle for reaction, the mol ratio of tertiary amine and methylcarbonate is 1:1～1:5,80～200 ℃ of temperature of reaction, reaction times 1～10h.The building-up reactions formula is as follows:
The synthetic of described bicarbonate quats salt is carbonic acid mono-methyl quaternary ammonium salt generation hydrolysis reaction, and the mol ratio of carbonic acid mono-methyl quaternary ammonium salt and water is 1:1～1:10,20～90 ℃ of temperature of reaction, reaction times 1～7h.The building-up reactions formula is as follows:
The synthetic of described other gegenion quaternary ammonium salt is that carbonic acid mono-methyl quaternary ammonium salt and various organic acid, mineral acid and alkali react in methanol solvate, carbonic acid mono-methyl quaternary ammonium salt is 1:0.6～1:2 with the mol ratio of acid (alkali), 10～60 ℃ of temperature of reaction, reaction times 2～7h.The building-up reactions formula is as follows:
Synthetic of the present invention has novel trans ionic quaternary surfactant and has the surfactivity better than conventional surfactant; Synthetic method of the present invention has adopted green chemical industry material carbon dimethyl phthalate, avoided product toxic raw material residual, has reduced product to the murder by poisoning of human body with to the pollution of environment.
Embodiment
Below in conjunction with embodiment the present invention is made an explanation.
Embodiment 1
Take by weighing 21g dodecyl dimethyl tertiary amine and 18g methylcarbonate, join in the 100mL reactor, slowly be warming up to 105 ℃, stirring reaction 2h.Reaction naturally cools to room temperature after finishing, and collects product, and recrystallization obtains dodecyl trimethylammonium methyl carbonate ammonium white solid.Take by weighing 3g dodecyl trimethylammonium methyl carbonate ammonium and 10g water, join in the 50mL flask, 30 ℃ of stirring reaction 5h.After reaction finished, concentrated, recrystallization obtained dodecyl trimethylammonium bicarbonate of ammonia white solid.
Embodiment 2
Take by weighing 12g octadecyl dimethyl tertiary amine and 16g methylcarbonate, join in the 500mL reactor, slowly be warming up to 110 ℃, stirring reaction 3h.Reaction naturally cools to room temperature after finishing, and collects product, and recrystallization obtains octadecyl trimethylammonium methyl carbonate ammonium white solid.Take by weighing 4g octadecyl trimethylammonium methyl carbonate ammonium and 9g water and join in the 50mL flask, 30 ℃ of stirring reaction 5h.After reaction finished, concentrated, recrystallization obtained octadecyl trimethylammonium bicarbonate of ammonia white solid.
Embodiment 3
Take by weighing 15g dodecyl dimethyl tertiary amine and 16g methylcarbonate, join in the 100mL reactor, slowly be warming up to 105 ℃, stirring reaction 2h.Reaction naturally cools to room temperature after finishing, and collects product, and recrystallization obtains dodecyl trimethylammonium methyl carbonate ammonium white solid.Take by weighing 5g dodecyl trimethylammonium methyl carbonate ammonium and 1g acetate, join in the 50mL flask that 10mL methyl alcohol is housed 35 ℃ of stirring reaction 4h.Reaction finishes the back underpressure distillation and removes methyl alcohol, and recrystallization obtains dodecyl trimethylacetic acid ammonium white solid.
Embodiment 4
Take by weighing 16g tetradecyl dimethyl tertiary amine and 15g methylcarbonate, join in the 100mL reactor, slowly be warming up to 110 ℃, stirring reaction 3h.Reaction naturally cools to room temperature after finishing, and collects product, and recrystallization obtains tetradecyl trimethylammonium methyl carbonate ammonium white solid.Take by weighing 5g tetradecyl trimethylammonium methyl carbonate ammonium and 1g acetate, join in the 50mL flask that 10mL methyl alcohol is housed 35 ℃ of stirring reaction 4h.Reaction finishes the back underpressure distillation and removes methyl alcohol, and recrystallization obtains tetradecyl trimethylacetic acid ammonium white solid.
Embodiment 5
Take by weighing 15g dodecyl dimethyl tertiary amine and 16g methylcarbonate, join in the 100mL reactor, slowly be warming up to 110 ℃, stirring reaction 2h.Reaction naturally cools to room temperature after finishing, and collects product, and recrystallization obtains dodecyl trimethylammonium methyl carbonate ammonium white solid.Take by weighing 4g dodecyl trimethylammonium methyl carbonate ammonium and 6g lauric acid, join in the 50mL flask that 18mL methyl alcohol is housed 45 ℃ of stirring reaction 4h.Reaction finishes the back underpressure distillation and removes methyl alcohol, and recrystallization obtains dodecyl trimethylammonium ammonium laurate white solid.
Embodiment 6
Take by weighing 20g tetradecyl dimethyl tertiary amine and 15g methylcarbonate, join in the 100mL reactor, slowly be warming up to 110 ℃, stirring reaction 3h.Reaction naturally cools to room temperature after finishing, and collects product, and recrystallization obtains tetradecyl trimethylammonium methyl carbonate ammonium white solid.Take by weighing 5g tetradecyl trimethylammonium methyl carbonate ammonium and 4.2g lauric acid, join in the 50mL flask that 10mL methyl alcohol is housed 45 ℃ of stirring reaction 4h.Reaction finishes the back underpressure distillation and removes methyl alcohol, and recrystallization obtains tetradecyl trimethylammonium ammonium laurate white solid.
Claims (9)
1. alkyl trimethyl quaternary ammonium salt is characterized in that chemical structural formula is as follows:
In the formula: R is C
1～C
22Saturated, unsaturated, straight chain, the alkyl of side chain;
A
-Be CH
3CO
3 -, HCO
3 -, HCOO
-, CH
3COO
-, lactate, laurate, cardamom acid group, stearic acid root, HSO
4 -, NO
3 -, H
2PO
4 -, OH
-
2. alkyl trimethyl quaternary ammonium salt according to claim 1 is characterized in that: the gegenion of quaternary ammonium salt partly is CH
3CO
3 -, HCO
3 -, HCOO
-, CH
3COO
-, lactate, laurate, cardamom acid group, stearic acid root, HSO
4 -, NO
3 -, H
2PO
4 -, OH
-Deng.
3. alkyl trimethyl quaternary ammonium salt according to claim 1, it is characterized in that: come carbonate synthesis mono-methyl quaternary ammonium salt with methylcarbonate as quaternizing agent, synthesize quaternary ammonium salt by hydrolysis reaction or with various acid (alkali) generation replacement(metathesis)reaction again with other gegenion.
4. the synthetic method of quaternary ammonium salt according to claim 3 is characterized in that: alkyl dimethyl tertiary amide and methylcarbonate generation quaterisation, and carbonate synthesis mono-methyl quaternary ammonium salt, the building-up reactions formula is as follows:
5. the synthetic method of quaternary ammonium salt according to claim 3 is characterized in that: carbonic acid mono-methyl quaternary ammonium salt generation hydrolysis reaction, and synthetic is the quaternary ammonium salt of gegenion with the bicarbonate radical, the building-up reactions formula is as follows:
6. the synthetic method of quaternary ammonium salt according to claim 3, it is characterized in that: carbonic acid mono-methyl quaternary ammonium salt and various organic acid, mineral acid and alkali reaction, synthetic gegenion are HCOO
-, CH
3COO
-, lactate, laurate, cardamom acid group, stearic acid root, HSO
4 -, NO
3 -, H
2PO
4 -, OH
-Quaternary ammonium salt, the building-up reactions formula is as follows:
7. the synthetic method of carbonic acid mono-methyl quaternary ammonium salt according to claim 4 is characterized in that comprising following reaction conditions: the mol ratio of tertiary amine and methylcarbonate is 1:1～1:5,80～200 ℃ of temperature of reaction, reaction times 1～10h.
8. the synthetic method of hydrogen-carbonate quaternary ammonium salt according to claim 5 is characterized in that comprising following reaction conditions: the mol ratio of carbonic acid mono-methyl quaternary ammonium salt and water is 1:1～1:10,20～90 ℃ of temperature of reaction, reaction times 1～7h.
9. the synthetic method with other gegenion quaternary ammonium salts according to claim 6 is characterized in that: react in methanol solvate, carbonic acid mono-methyl quaternary ammonium salt is 1:0.6～1:2 with the mol ratio of acid (alkali), 10～60 ℃ of temperature of reaction, reaction times 2～7h.
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| CNA2008101725239A CN101372457A (en) | 2008-10-29 | 2008-10-29 | Preparation of alkyl trimethyl quaternary ammonium salt |
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|---|---|---|---|
| CNA2008101725239A CN101372457A (en) | 2008-10-29 | 2008-10-29 | Preparation of alkyl trimethyl quaternary ammonium salt |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102806046A (en) * | 2012-08-24 | 2012-12-05 | 四川大学 | Green preparation method of quaternary ammonium salt surfactant |
| CN103547584A (en) * | 2011-06-17 | 2014-01-29 | 流体公司 | Synthesis of hetero ionic compounds using dialkylcarbonate quaternization |
| CN107400043A (en) * | 2016-05-20 | 2017-11-28 | 中国科学院过程工程研究所 | Application and propylene glycol synthetic method of the ionic liquid in propylene glycol synthesis |
| CN108689891A (en) * | 2018-06-29 | 2018-10-23 | 广州市润研基因科技有限公司 | A kind of synthetic method of quaternary ammonium salt |
| CN109320420A (en) * | 2018-11-16 | 2019-02-12 | 厦门医学院 | A kind of synthetic method of chain alkyl methyl carbonate quaternary ammonium salt |
| CN112916211A (en) * | 2019-12-05 | 2021-06-08 | 宁波行殊新能源科技有限公司 | Mineral agent for flotation of lithium potassium sulfate |
| CN115109337A (en) * | 2022-07-11 | 2022-09-27 | 江苏立晟德新材料有限公司 | Plastic product semiconductive sheath material for preventing rats, ants and insects |
-
2008
- 2008-10-29 CN CNA2008101725239A patent/CN101372457A/en active Pending
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103547584A (en) * | 2011-06-17 | 2014-01-29 | 流体公司 | Synthesis of hetero ionic compounds using dialkylcarbonate quaternization |
| CN103547584B (en) * | 2011-06-17 | 2017-02-15 | 流体公司 | Synthesis of hetero ionic compounds using dialkylcarbonate quaternization |
| CN102806046A (en) * | 2012-08-24 | 2012-12-05 | 四川大学 | Green preparation method of quaternary ammonium salt surfactant |
| CN107400043A (en) * | 2016-05-20 | 2017-11-28 | 中国科学院过程工程研究所 | Application and propylene glycol synthetic method of the ionic liquid in propylene glycol synthesis |
| CN107400043B (en) * | 2016-05-20 | 2020-12-29 | 中国科学院过程工程研究所 | Application of ionic liquid in synthesis of propylene glycol ether and synthesis method of propylene glycol ether |
| CN108689891A (en) * | 2018-06-29 | 2018-10-23 | 广州市润研基因科技有限公司 | A kind of synthetic method of quaternary ammonium salt |
| CN108689891B (en) * | 2018-06-29 | 2021-07-30 | 广州市润研基因科技有限公司 | Synthesis method of quaternary ammonium salt |
| CN109320420A (en) * | 2018-11-16 | 2019-02-12 | 厦门医学院 | A kind of synthetic method of chain alkyl methyl carbonate quaternary ammonium salt |
| CN112916211A (en) * | 2019-12-05 | 2021-06-08 | 宁波行殊新能源科技有限公司 | Mineral agent for flotation of lithium potassium sulfate |
| CN115109337A (en) * | 2022-07-11 | 2022-09-27 | 江苏立晟德新材料有限公司 | Plastic product semiconductive sheath material for preventing rats, ants and insects |
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Application publication date: 20090225 |